CASCO BAY, Maine — The omnipresent fog didn’t bring me down. It made my experience on the Casco Bay islands more authentic. I was here to explore the cluster of islands just minutes from downtown Portland. Even when the fog grew thicker than coagulated clam chowder, I forced a smile while straining to see through the mist and gloom.
Maine, the way fog should be.
But my smile melted away when the torrential rains began. On my first day here, I kayaked from Portland to Fort Gorges, an imposing Civil War-era granite citadel perched on Hog Island Ledge in the middle of the bay. The fort, which was constructed during the Civil War but never saw battle, is on the National Register of Historic Places and open to visitors. By the time my kayak tour group came upon the 19th-century fort, thunder clapped in the distance. We were mere feet away from the fort — at least I think we were, I couldn’t tell in the fog — and were told to turn back.
That may not sound like a ringing endorsement, but despite the inclement weather, the Casco Bay islands are unique. You can take the Casco Bay Lines ferry from Portland to six islands and find yourself transported from the hip downtown restaurants to petite family-run lobster shacks and remote nature trails in minutes, all for around $10 round trip. You can bring your car on some routes, but I managed fine without one.
The islands are rustic, rural, and incredibly peaceful after the ferries full of day-trippers have finished their routes. Long before I saw the weather forecast, I planned to visit three islands, specifically those with grand old hotels: Chebeague Island, Peaks Island, and Great Diamond Island.
Chebeague (pronounced sha-big) is geographically the largest of the islands not connected to the mainland by a bridge. It’s just over 3 miles long and has a lovely grand dame hotel, the Chebeague Island Inn, a golf course, and a blink-and-you’ll-miss-it town center.
The inn is located on a hill overlooking the ocean. It faces west, and I was told it has a gorgeous view of the sunset from the wraparound porch. I had to use my imagination to picture the sun painting the evening sky with swaths of orange and pink. I’d never stayed in a hotel room that was truly boho chic before Chebeague Inn, but this was the real deal. My room was painted all white, even the old wood floors were white. Contrast that with modern art adorning the walls and a Queen Anne chair with dramatic seashell upholstery and you get the vibe. Think of it as a Maine island hotel by way of Soho. Rates during the summer hover at $269 a night. If you don’t stay over, you can still grab dinner at the inn and easily see the island in less than a day.
The inn has the best restaurant on the island. Lobster would have been the most logical dish to order. It comes directly from the nearby dock. But I spotted a delicacy called pollack schnitzel on the menu. I always feel compelled to order anything made with brown butter emulsion. Unlike it’s porcine cousin, the pollock schnitzel felt far healthier as it tenderly flaked under my fork. If you stay at the inn overnight, the blueberry pancakes are a necessity. Don’t even pretend you want yogurt, just get the pancakes.
It rained through dinner, but the following morning, the fog appeared to be burning off. After pancakes, I optimistically grabbed one of the hotel’s bikes and pedaled before the precipitation had a chance to return. I rode through an incredibly quaint downtown and continued to a handful of tiny (and deserted) beaches. There are beaches on the Casco Bay islands, some quite nice, but if you’re planning an extended beach vacation, I would likely stick to the large sandy beaches south of Portland. I found the islands best for hiking, relaxing, and eating. Not necessarily in that order.
I opted for a self-directed hike to the scenic rocks at Deer Point to finish off my time here. It was the perfect place to eat my sandwich from Doughty’s Island Market.
As my ferry approached Peaks Island, I thought I saw sun, but it was difficult to tell through the orange haze of the Canadian wildfire smoke. But there was no rain (hurrah!), and I was ready to explore. The ferry ride to Peaks Island, which is approximately 15 minutes, will set you back $7.70 round trip from Portland. The island is a metropolis compared to Chebeague. There are a few art galleries, a handful of restaurants and shops, the inn, and, most importantly, Down Front, an ice cream shop that has heavenly moose tracks ice cream.
As I learned from my ill-fated kayaking voyage to Fort Gorges, Casco Bay was once a hotbed of military activity. The 5th Maine Museum was built as a social hall by the veterans of a local volunteer Civil War Regiment. It now houses a museum that looks at the history of Peaks Island, plus the Civil War and the island’s role in WWII. There’s more war history at Battery Steele, a concrete structure that was used as a coastal gun battery during World War II. It’s now empty and the long, dark interior rooms are covered in graffiti. It’s the kind of place where you might see Leatherface and his family staying for a respite between chainsaw murders. Bring a flashlight if you decide you want to do some creepy exploring.
I skipped Battery Steele because I was more interested in trying the local seafood than getting murdered. The Island Lobster Company is a “trap-to-table” restaurant with staples such as lobster rolls and whoopie pies. When I arrived for a late lunch, there was casual day drinking and fried food all around me. I was craving a clam roll, and it arrived in a perfectly toasted golden bun with a small mountain of crisp fried clams. I returned to collapse in my room at the Inn on Peaks Island.
The Inn on Peaks Island has eight suites, so unlike the 41-room Chebeague Island Inn, it tends to book quickly. The largest suite sleeps 16 (that’s not a typo), and goes for about $1,000 a night during summer. I choose the lovely Chebeague Island Suite, which sleeps two for $350 a night. I’m normally not a TripAdvisor kind of guy, but I opted for the number one restaurant on the island (that’s out of three eateries), the Cockeyed Gull. I was expecting another fried seafood clam shack, but the Inebriated Gull, as I renamed it, has a menu with dishes such as jerk chicken bites, cheesesteak, and almond-encrusted haddock. There’s also a beautiful terrace outside. I opted for inside, as the rain and fog decided it wasn’t done with me.
As with all the bay islands, there are a finite number of activities. On Peaks Island, you can locate most offerings as soon as you disembark the ferry. One of those activities is the kookiest place I’ve ever seen, which is really saying something. The Umbrella Cover Museum which pays homage to the sleeves that cover umbrellas, holds the Guinness Book of World Records title for the largest collection of umbrella covers in the world. There are more than 2,000.
The star of the museum is Nancy 3. Hoffman. Yes, her middle name is the numeral 3. She finds any excuse to bust out her accordion and start singing the museum’s two theme songs, because every museum should have two theme songs. If you ask nicely, she’ll play selections from her CD of umbrella-related songs. I immediately asked for Rihanna’s “Umbrella,” which she does not know. I asked for the Carpenters’ “Rainy Days and Mondays,” but she didn’t have it memorized. Instead she sang the love theme from the 1964 film “The Umbrellas of Cherbourg” with lyrics that she created herself. I decided my time on Peaks Island was over, primarily because I was afraid that Hoffman might track me down and start playing her accordion again.
GREAT DIAMOND ISLAND
As my island adventures were nearing an end, the sun decided to pay a visit. I ended on Great Diamond Island, which offers little in the way of commercial activities, but much in the way of relaxation. There are no cars, with the exception of a few commercial vehicles. People traverse the island by golf cart. It’s dominated by brick barracks that were once home to Fort McKinley, a base constructed to defend Portland Harbor during the Spanish-American War. There is a museum where you can learn more about the island’s military past.
The brick barracks, constructed at the turn of the last century, are now condos that overlook a charming town common. These long brick structures and their surrounding grounds are private, and there are signs on every corner to remind you. The luxurious Inn at Diamond Cove also served as a military barracks.
I’d describe the Inn at Diamond Cove as more of a retreat or resort than an inn because of its peaceful surroundings and remote nature. The price also reflected its posh nature. Summer rates flirt with $450 night. I’d recommend spring or fall, which runs a more reasonable $250 a night. But remember, you can day trip to any of the islands. In the case of Great Diamond Island, take the ferry to Diamond Cove, and you can easily cover the entire island in less than a day.
I opted to use my time to sit by the pool at the inn, which I considered work because I needed to make sure it was suitable for readers. My verdict is that it was more than suitable. But with the sun blazing, I had time to hike and linger on the beaches. Diamond Cove beaches are dominated by pebbles, but they’re tucked away. You can bring a beach chair or towel and watch the boats buzz through the bay. After a week of fog, I took this as my reward. I decided the Fort McKinley Museum could wait, at least until the fog found me again or Nancy 3. Hoffman showed up with her accordion.